Session summaries beat context decay like coffee beats my ability to function

I used to just let conversations run until Claude started contradicting itself three turns back, which is a great way to debug your own debugging. Then I'd paste the entire mess into a new session and hope it read faster than I type. Spoiler: it didn't, and I'd lose the thread anyway while Claude re-indexed my life story.

So now I cap sessions at around 65 percent of the window and write a summary before context gets stale. The summary has to be ruthlessly concrete: what we built, what broke, what the actual code looks like now, what we're trying next. I paste that summary as the first message in the next session instead of pasting twelve turns of my increasingly delirious questions.

With Claude Code or Cursor, I just write "---SUMMARY---" in my notes at the midpoint, then force myself to actually write it out. The session ends, I start fresh, paste the summary, and we pick up without me re-explaining why I thought TypeScript generics were optional. The next session stays sharp because the context is distilled, not diluted.

The catch is this only works if your summary is actually useful. If you write "continued on the file" and nothing else, you're just making the next session mad at you. Also, some problems genuinely need the full conversation history, especially when you're debugging why someone else's legacy code exists. Summaries help, but they're not magic for gnarly interdependencies.